A visit to the Vatican takes up much of the day in itself, and yet that’s only the tip. Naturally, you can’t leave Italy without having seen the Pantheon, Piazza Navona, the Trevi Fountain, and the Spanish Steps. Fortunately they’re all within walking distance, and with the exception of the interior of the Pantheon, you can, and should, see those spotlit sites in the evening, gelato in hand, after an aperitif in Campo de’ Fiori and a pizza in the alleyways between there and Piazza Navona. I would save daylight hours for a morning walk or inline skating in the Villa Borghese and exploring the neighborhood near the Colosseum: the crypts beneath San Clemente, the recently discovered Roman Houses nearby, and the Domus Aurea, Nero’s underground palace, if it’s not under restoration. Day 3: Montalcino, Montepulciano, Siena, and Chianti This is going to be an eating and driving day. Obviously you could and should spend a week in this part of Tuscany, but the basics are to see some vineyards, pick up a collection of wine, and spend the evening in one of Chianti’s lovely agriturismi.